Oakland Vacations from $359

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Your Oakland Vacation

From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.

The Latest Oakland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG
Wyndham Grand Pittsburgh Downtown
DoubleTree by Hilton Pittsburgh Airport
Omni William Penn Hotel
Fairmont Pittsburgh

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland

Oakland Hotel Deals

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $158 total per night from Oct 19 to Oct 20
$158 total
Oct 19 - Oct 20
Total with taxes and fees
8.8/10 Excellent! (460 reviews)
"Great stay. Thank you!"

Reviewed on Sep 30, 2025

Courtyard by Marriott Pittsburgh University Center
Hotel Indigo Pittsburgh University-Oakland by IHG

Hotel Indigo Pittsburgh University-Oakland by IHG

3.5 out of 5
329 Technology Drive, Pittsburgh, PA
Fully refundable
$112 nightly
The price is $127 total per night from Nov 3 to Nov 4
$127 total
Nov 3 - Nov 4
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"The room is very up-to-date and very comfortable. There is plenty of space, too."

Reviewed on Oct 6, 2025

Hotel Indigo Pittsburgh University-Oakland by IHG
The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
5130 Bigelow Boulevard, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $242 total per night from Nov 9 to Nov 10
$242 total
Nov 9 - Nov 10
Total with taxes and fees
9/10 Wonderful! (691 reviews)
"10/10"

Reviewed on Sep 29, 2025

The Oaklander Hotel, Autograph Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.